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I do not understand. When you write, "earned his stripes," what exactly do you mean?

It's a military reference. Sergeants (I think) have a striped insignia, and it would mean a bump in rank (experience, knowledge, skill).

Edit: Not to say he was in the military, it's a metaphor for how Walton gained experience and 'rank' in retail.

Incidentally, he did serve in the military. :)

That was his first success as an entrpreneur, selling a Ben Franklin franchise store - http://en.wikipedia.org/wiki/Sam_Walton#The_first_stores